


Constellation

by Tintentrinkerin



Category: Supernatural
Genre: Abusive Parents, Alternate Universe - Modern Setting, Anal Sex, Angst and Romance, Bottom Dean Winchester, Dean's name is Dean Winchester, Dirty Talk, Double Penetration, Escort Sam Winchester, FTM, Friends With Benefits To Lovers, Guitarist Dean Winchester, Jack Kline & Claire Novak Friendship, Loss of Virginity, M/M, Mild Kink, Multi, Penis In Vagina Sex, Polyamory, Possible triggering language, Sam's name is Sam Campbell, Sex Toys, Threesomes, Top Sam Winchester, Transgender Jack Kline, Unrelated Winchesters (Supernatural), Versatile Jack Kline, pansexuality, transphobic parents
Language: English
Status: In-Progress
Published: 2021-03-14
Updated: 2021-03-14
Packaged: 2021-03-22 11:00:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,794
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30037674
Author URL: https://archiveofourown.org/users/Tintentrinkerin/pseuds/Tintentrinkerin
Summary: Jack Kline just wants to piss off his parents by spending 2,5k on an escort boy called 'John Wesson' to accompany him to a family dinner. That he would fall for the escort wasn't part of the plan. Also, that he gets to know the escort's friend Dean. All three will learn their lessons in courage, intimacy and leaving old patterns behind.
Relationships: Jack Kline/Dean Winchester/Sam Winchester
Comments: 2
Kudos: 7





	Constellation

**Author's Note:**

  * For [Therealgaybird](https://archiveofourown.org/users/Therealgaybird/gifts).



> In this fanfic, Jack Kline is ftm trans*.  
> I planned and wrote this fic after I've talked to several trans and non binary people, which was a big help. It also showed me the variety and possible dangers and triggers to LGBT people. This is why I will put this warning here again:  
> This fic might contain triggering language for people who are trans, enby or queer. Jack Kline IS comfortable with biological female terms for his body parts, you WILL find words like vagina and pussy here. Jack Kline is comfortable with P in V sex, as he's still discovering his identity and sexuality - and very curious.   
> IF YOU ARE UNCOMFORTABLE WITH / TRIGGERED BY FEMALE TERMS OF ANATOMY, DO NOT READ THIS FIC - I plan on MAYBE publishing the fic with gender neutral language upon request.
> 
> I gift this fic to the person who sent me a prompt a few weeks ago, asking for more fics about "Jack with a vagina". I wrote this fic for their entertainment and enjoyment first. I hope you will like it ❤

**Constellation**

“A group of stars forming a recognizable pattern that is traditionally named after its apparent form or identified with a mythological figure.”

( [ https://www.lexico.com/definition/constellation ](https://www.lexico.com/definition/constellation) )

_ Katy, we’d like to remind you about your grandpa’s 80th birthday barbeque next weekend. You may bring a friend. Love, Mom _

Jack sighs heavily when he reads the text he just received. Of course, his mother must deadname him, disrespect and belittle him. It’s something he is sadly used to since he came to terms with his own gender identity - that his family will never accept it, let alone show him some decency or respect. It used to make him cry, really get to him, soak his soul and ruin his day, but now, a year in the process of his social transition and counselling, he’s able to let the feelings come and go like a wave, like the tide. He might feel like he’s gonna drown in his sorrow and the sheer ignorance his family treats him with, but he’s learned to let it pass. It takes a lot of strength to fight his battle anyway, he doesn’t see any point in trying to change people who don’t want to be changed. He could just not show up to the barbeque, but as long as he’s in the position that he needs the financial help of his family, he doesn’t dare rebel too much. 

He’s close to graduating, studying is time consuming, his part-time job doesn’t pay enough. He’s decided to take the offenses on the chin for now, but as soon as he finds a job in the field he wants, he’ll cut ties, and never let his family back into his life again unless they apologize, feel real remorse about the oppression and the emotional abuse they inflicted. And since Jack knows that is not going to happen  _ ever _ , he already mentally said goodbye to them. He will be at the barbeque physically, but emotionally, he is not their offspring anymore. And, he thinks, they’ll think the same as soon as he makes up his mind about medically transitioning - the hormones, the surgeries. 

Nick and Kelly Kline raised Katy, a daughter.

But Jack has never been a daughter, he’s always been a son. He might have realized it at the age of 21, but it doesn’t change that fact. He’s trans. He’s always been trans. And his family are raging conservative Christians, living the conservative filthy-rich country club life. And their daughter is ‘one of  _ them _ ’. That’s what they call people out of the binary, out of the norm.  _ ‘Them’ _ . They say it like an insult. With disgust. And a portion of pity. As if Jack is sick. Infected with leprosy. Or the plague. In their eyes, Jack should be glad they haven’t disowned him yet. They pay for his counselling because they hope it will cure him of this sickness, but it won’t. 

Jack is **not** sick. Jack is finally exploring himself. Finding out who he is. 

With another sigh he sends a reply to his mom that just states he will come, and he will indeed bring a friend. He doesn’t quite know who to bring. He has friends at university. He’s not overly popular or anything, he likes being on his own, but he attends a queer pub moot every now and then and finds comfort in his queer friends’ stories and their understanding, tolerant, cheerful support. 

There’s still a tab open on his laptop, his mother really managed to message him when he was spending money on useless (or at least not really necessary) stuff with Daddy’s gold credit card. It was his way of quiet revenge. Nick never really checked what Jack did with the credit card, there was no limit. Usually the ‘pocket money’ they gave him besides paying for his apartment (their precious daughter shouldn’t live in a dorm with others!) was enough to get along, but the part time job helps Jack to save money actively to move out of here when he graduates and find a place for his own. Something that wasn’t paid for by mom and dad. Being dependent sucks. 

To sweeten the sucky situation Jack browses several pages of clothing for trans and non binary people, he needs a new binder, he also just found another gym where he could work out, also he needed several books for his classes. 

Wanting an even bigger ‘fuck you’ to his parents, he also opened a tab to shop for sex toys. He wouldn’t buy  _ that _ with Nick’s credit card, he would have to choose a billing service that makes the payment as neutral as possible. He doesn’t know exactly what his parents think of sex, but he guesses they sleep with their hands on top of the covers and only had sex enough to conceive him and his older sister. He can’t risk an act of pettiness backfiring and wind up with Nick cancelling the credit card. 

There’s a lot of nice things he’d like to buy. Vibrators and wands in all shapes and colors, and he adores some of the harnesses and strap ons he sees. As a bloody virgin and an awkward single in the middle of an identity crisis he’s not sure he’ll ever find someone to sleep with him.

So many people talk about tops and bottoms and verses and ‘sides’ and preferences and Jack is still very much untouched. But seeing these strap-on dildos makes him squirm, partly because he feels a faint euphoria about having an actual cock, but the thought of bottoming is also… Jack sighs, feels himself getting a little excited. Maybe, just maybe, … A harness and a dildo are added to his cart, also a new clitoral vibrator, and, because Jack likes to keep his toys as clean as possible, condoms and disinfectant spray. He picks express delivery, anxious to get his new toys despite not having anyone to use them with. He can always just wear the harness and strap in private, look at himself in the mirror and enjoy actually feeling good about his body, for once. 

Lost in thought, Jack opens a tab with an erotica website for queer people, because he can’t stand watching conventional sexist porn. When he notices an advertisement on the bottom of the page leading to an escort service called  _ Eden Boys Escorts _ , he gets a very naughty idea, and clicks on the link.  _ Please don’t let it be spam _ , he thinks, but he’s lucky. It’s an actual page, though he can’t judge how serious and authentic it is since he’s never visited such a website before, but it looks very appealing. It’s a gay escort service. Why not spend daddy’s money on a person to act as his boyfriend at the stupid family barbeque? That would be some petty revenge, and that was exactly what Jack was in the mood for. 

Closer inspection reveals that there’s a lot of variety in the escorts, but they all look disappointingly flawless. Six packs, tanned, strong arms, shaved faces and bulges in their pants that promise a ‘package that will pleasure you beyond expectations’. They look like they stuffed socks in their pants. There’re not only hunky men, but so many, so so many twinks; hairless and slender, pale, and faces that look like some of them shouldn’t even be allowed to do sex work because they’re most definitely underage. The advertisement blocks are super cheesy, all about the good looks and the missing gag reflexe., Everything is so binary, made for cis gay men, and the joy Jack felt at first fades, and he starts to feel slightly uncomfortable looking at these men as if they’re just pieces of meat. He didn’t want to hire an escort just to piss off his parents that would give off the impression he was a paid companion for the day. But now the damn thought is in his head, he can’t get it out.

He is just about to close the browser tab when a pop-up shows up right over the curriculum of the boy “Austin,” who is described as a ‘bottom, subby delight who will take your dick with anticipation and the sweetest moans’ - ugh,  _ no _ \- but this pop-up looks very different from the rest of the site. It’s advertising another escort page but, this one, it looks genuinely intriguing 

It reads ‘ **_John Wesson, independent queer escort_ ** ’ - Jack is hooked immediately. 

_ If this is a scam now, I will close the tabs and never think about this shit again _ , Jack promises himself and then clicks the link.

It looks serious. Not really like a scam. It’s a simple page that just says “John Wesson Queer Escort” as a header. The background is a black and white photograph of a man tying someone’s wrists together with something that looks like a silk ribbon. The photo is cropped so that it doesn’t show faces or more naked skin than just a bare, very defined, male chest and the hands being bound together. It looks classy, not at all cheesy like at the website of the  _ Eden Boys _ . Jack is surprised and pleased about this, he feels comfortable looking at this wonderfully arranged photo. And then, just below the header of the website there is also a photo of said John Wesson and -  _ oh boy _ .

_ He is handsome. _

Jack gulps. This man is definitely not one of those barely legal twinks from the other site, this is a grown man with hazel eyes, wonderful brown hair, a little scruff, but not too much, and the way he glances at the camera - it looks warm and caring. He gives him sheer puppy dog eyes. The short introduction text doesn’t reveal much about the escort: 

_ Hello,  _

_ My name is John Wesson and I'm an independet queer escort resident in Palo Alto, California. Please use the navigation below to get to know me, my lifestyle and my price list.  _

_ I hope to hear from you soon. _

_ Love, John. _

He doesn’t look like a ‘John’ for Jack, too young for that, but on the other hand ‘John’ is a very common name, the second most common name in the United States, probably also in Great Britain and other countries with English as the official language. It dawns on him that this is probably an alias and an escort wouldn’t put their legal name on this website and reveal personal information to strangers. Jack scrolls further down and clicks the link to John’s price list. Something that Jack needs to know first. How much will it cost to piss his parents off?

The price list isn’t long but it doesn’t need to be. One hour spent on a date would be $500. Already, Jack gets a bit dizzy. The price for 12 hours or one whole night is $2,500 and there’s even a price for a whole week. Booking ‘John’ for a whole week would be $10,000. 

And since this is an independent escort who’s not affiliated with an agency that is probably very very good value, because an agency would probably charge fees and would also retain a percentage share of the profit an escort makes. That’s what Jack assumes, anyways, having zero experience in that field. Maybe he would have to pay double for an escort from Eden Boys. But ‘John’ is so incredibly handsome, and he looks like someone Jack would feel comfortable with, and that’s why he returns to the landing page and opens the Rules page to learn about what is needed to hire this escort. Not that Jack is sure yet, 2.5k is still  _ a lot _ and Nick would definitely notice such a big charge on the credit card.Jack would either have to transfer or withdraw from the credit card in smaller increments. Either way, that much money is more than Jack had imagined it would be. Maybe he won’t do it after all. But , now that he’s here, he wonders what kind of rules an escort would have. 

  * _The full charge must be transferred via bank transfer or an online billing system (stated below)._


  * I accept inquiries via phone, email and the contact form below. Please do not text my mobile number as it’s only registered for calls.


  * If you make an inquiry via email or contact form, please include information about the date, the length of your to-be-booked service, the place, dresscode, etc. 


  * Every accepted client needs to be tested recently for STIs (HIV inclusive). The test results shouldn’t be older than a month.


  * Clients must be at least 21 years old to book.


  * I only practice safe, consensual sex. Condoms are mandatory. Kinky sex is encouraged but must follow the common rules for kink (safewords, soft and hard limits).


  * If you decide to send an inquiry, please note that I need at least 24 hours to prepare. Spontaneous dates on the same day are sometimes not possible to provide. 


  * I offer my service to persons of any gender and sexual orientation.


  * I will only serve the person or people who hired me. My prices for dates with more than one client can be enquired for directly. 


  * In the event of cancellation with less than 24 hours notice, I will withhold 50% as compensation fee.



All of these are things that make sense to Jack. It sounds all like it’s business, but in the end that’s simply what it is. Business. It’s a service someone offers for money. Jack browses the biography he has linked on the landing page and after reading these rules. The text about his life sounds way more sensitive and also very welcoming. John states that he was born in 1990, which makes him 30 years old, 8 years older than Jack is. The text says he’s always lived in Santa Clara, CA but he moved closer to Palo Alto recently. He enjoys nerdy stuff a lot, he even goes into detail about his love for Lord of the Rings, true crime and Renaissance faires. His favorite band is Kansas, which makes Jack laugh, because, when were those guys popular? In the 70’s? But he’s not going to judge, he likes all different kinds of music, classic rock included. 

Instead of stating things like his height, weight, position in bed and which cologne he likes most, ‘John’ has listed his favourite book, favourite quote and favourite smell, which is very cute - the smell of old books. ‘John’ sounds like such a down to earth, laid back and funny kind of man, Jack would like to get to know him even if he wasn’t an escort that he’d found via pop-up. He also says he’s a vegetarian. And that he graduated from Stanford. His day job knows about his independent escort services and supports him ‘all the way’. That sounds really awesome. 

Jack is fascinated by this man, who on one hand offers services of dates with possible sex but sex is barely mentioned on the website itself. His sexuality, his preferences - none of that is shoved in Jack’s face and he’s very comfortable with this. There are some other pictures of several photoshoots but John is never naked in any of them. Okay, there are two photos of him that aren’t exactly _ fully clothed _ , one of him wearing lace panties (which is super hot and Jack gulps at the sight, painfully aware that he is still worked up and needs to deal with that soon) and one of him in only suit trousers, a belt in his big hands. Damn this man has huge hands. Strong arms, veins popping, a muscular chest. There’s a simple tattoo of a stylized crown on his arm but nothing extravagant. These two photos are the only reminder of whose page Jack is browsing. An escort’s. Who gets paid for company and sex. Jack can’t decide which he likes better, the lace panties photo or the belt photo, both make him all wet and squirmy. The fact that John is very open about his queerness, being a little kinky, and overall seems to be open and fuck gender roles, makes it an irresistible opportunity. Jack closes the tabs except the page with the contact form. At first he wants to fill out the form and send it, but something makes him grab his phone (11 messages in his study group, some notifications from social media and one match on a dating platform that he wanted delete ages ago but never did) and dial the number of ‘John Wesson’ and now he’s sure he wants to be the petty little asshole and spend daddy’s money on a callboy and he’s also a horny idiot who’s dying to hear the voice of a man he found online.


End file.
